A book that I very much enjoyed and could help you a lot is "Photographic Assignments" by Michael Busselle. It may be hard to find because it was printed in 1992 and reprinted in 1994. You can use it almost like a text book to give yourself all types of photographic assignments, as demonstrated in the book, and then carry them out. This will help get you in touch with what you like, photographically speaking, and probably make you a much better photographer in the process.

I would caution against buying any new equipment just yet. Camera are expensive and without knowing where you are headed, you chance of bad investments is high. But more important, the camera does not matter until you find it is the limiting factor in the direction you want to go. For example, suppose you end up liking street photography. It is very possible that the camera you have would be ideal, or perhaps a digital P&S.

Use the web, starting with this massive site, to learn and experiment.

Take some classes on photography. Many two and four year colleges have adult education classes or may allow you to audit a class or two. Art centers and schools, museums, zoos etc. offer adult education, that may include photography. Many of the instructors at these institutions will also do private lessons if the classes are not convenient. Some camera stores even offer photo classes to help get you started.

I teach at a local college and I'm always willing to talk to people wanting to improve their picture taking enjoyment.

I would make self assignments and go out and shoot them. Try to join other photographers since it is a lot more fun and easier to self discipline if you share your commitment with others. There is a great article by Michael Johnston somewhere in this site about self assignments. If you can afford it donīt try to go head in into making a living with photography. This will start happening on its own if you are walking the right steps. It is far more enjoyable to do it freely without big responsabilities on your shoulders.

I have always enjoyed taking pictures from the day my dad created a dark room and my first camera (a twinlens 120 ~ can't recall the name but alas have no more). I have always been more attracted to nature photos; animals, plants, shapes, shades, panoramics, etc...

I have dreams about expanding my hobby to something more, but I am not yet ready or willing to abandon my reality. And everything I have read warns against it for some reason or another... So I am looking for that fine line between reality and the dream; improve, explore, then see if this works for me.

What I am looking for is how to take my hobby beyond the pictures of the family camping trip, hike or bike ride to sharing/posting/selling it with the community and possibly making a dollar or two (and maybe at some point a living). I am unsure of what niche I like best so I would like to explore and see what I like and what sells. I also feel constrained by the point and shoot cameras that I own; I want to get closer (zoom or macro), shoot wider angles and use filters, etc... I like digital because I can take a lot of pictures without the cost of film.

With what do I take the pictures with; something that will allow me to grow and I can grow with (digital or film) ?

With whom do I share/sell it with ?

Can you recommend any Books or reference that will help with this challenge ?

The best way to improve your photography is to do it more. The best way I've found to jump start this is to go on a photography workshop with a good photographer. I have not been on one of Michael's workshops, but not for lack of trying. They are very popular. I have been on a couple with Steve Kossack and would highly recommend him. The other instructors on Michael's site would also likely be great. Bring whatever camera you are using and lots of film and or storage and just immerse yourself in photography for a few days. It's a great way to break the ice and get started. Here are a couple of links to photos I've taken on two workshops.

I have dreams about expanding my hobby to something more, but I am not yet ready or willing to abandon my reality. And everything I have read warns against it for some reason or another...

You will always hear warnings from people. But then again, no one ever achieved a dream by strictly obeying a warning. The task is to figure out what your dream is. There are so many ways to expand your hobby, you'll need to decide which is right for you. Do you want to be a commercial photographer? An occassional stringer for your local paper? Do you want to get in a local gallery or sell a few prints in a local coffee shop? Or do you want to be a high-powered fashion photographer? Many paths.

First thing, is to do a ton of research on the business of photography. I am always surprised at how many people try to start a business without "running the numbers" first. Get a spreadsheet and calculate the cost of an imaginary business (equipment, rent, supplies, product lines, potential profits).Talk to local pros. Ask lots of questions. Volunteer as an assistant to learn the ropes. Etc.

There are some good books by John Shaw on this, including Business of Nature Photography. Caroll Michels has a good one on the business of art, called How to Survive and Prosper as an Artist.

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With what do I take the pictures with; something that will allow me to grow and I can grow with (digital or film) ?

Shoot with what you have. Buy new equipment when you know exactly how it will improve your work, not on the hope that it will. It's always better to have less than more.

Get together with knowledgable photographers. Review their work. Get their ctritiques of your work. Make sure they are honest enough to tell you what is "good" and what needs work. Avoid the group that loves everything.